After struggling for years as an artist in New York City, Jake is calling it quits and returning home to Ohio. On his last day in the city, he persuades his three oldest friends to help him retrace their greatest adventure together: a walk down the entire length of Manhattan. But their attempt to reclaim the glory of their early 20s doesn't go quite as planned. Over the course of the day, buried conflicts emerge as Jake becomes embroiled with his ex-girlfriend and his friends dip into their own crises of manhood.